Since 2015, Hamilton has been a runaway Broadway hit, racking up record numbers and earning the Best Musical Theater Album honors at the 58th GRAMMY Awards. This week, the musical's playwright/composer Lin-Manuel Miranda released a moving music video for a song from last year's Hamilton Mixtape.

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Led by Somalian-born artist K'naan, "Immigrants (We Get The Job Done)" is based on a song from the show "Yorktown (The World Turned Upside Down)," and the video features members of the cast with special appearances by a team of rappers including Snow Tha Product, Riz MC, and Residente of the 20-time Latin GRAMMY- winning  group Calle 13. 

The powerful message behind the lyrics and video shine a light on the struggle immigrants still face, reminding viewers that America is both founded on and fueled by immigrants' hard work and ingenuity, a message mirrored in the stage show.

In addition to the new video, Miranda announced a contest on Prizeo in conjunction with his #Ham4all campaign. With a $10 donation to Miranda's Immigrants: We Get The Job Done Coalition, contestants enter a drawing for a trip to Los Angeles to see Hamilton and experience a private meet-and-greet with Miranda himself.

Stevie Wonder, Taylor Swift, "Hamilton: Watch Great GRAMMY Acceptance Speeches

For years, Jasmine Cephas Jones never saw herself as a recording artist.

As a teen, she attended multiple meetings with producers, but nothing felt authentic. In her twenties, she went the Broadway route, securing the dual role of Peggy Schuyler and Maria Reynolds in the original cast of Lin-Manuel Miranda's Hamilton. And even after she created her debut EP, Blue Bird, in 2020, Cephas Jones' future was still uncertain; the pandemic happened, and a string of hard moments left her wondering what would be next — and what would become of her music. 

Even so, her creativity was booming. She wrote and recorded an entire album's worth of music alongside seven trusty collaborators, including Blue Bird producer Zach Golden and Samora Pinderhughes, who co-wrote a track on Blue Bird and produced Phoenix. Nearly four years later, that project finally gets to see the light of day: her debut album, fittingly titled Phoenix. 

The 13-track LP started as a story of romance. But as Cephas Jones sat with the songs, she discovered her most fulfilling relationships were found in her family, friends, collaborations, and artwork, offering an entirely new meaning of connection and perseverance. As a result, Phoenix is a patchwork of her life, and every formative moment in her musical upbringing: It's her mother's love of Stevie Wonder's witty lyricism on "Bad Habits," her father's penchant for Prince's genre-bending production on "Fade in the Water," and her years of opera training on "Cali." As Cephas Jones puts it, it "just sounds like me."

Before Phoenix arrived on May 30, Jasmine Cephas Jones sat down with GRAMMY.com to discuss how she grew from the bluebird into the phoenix, and to revisit the moments throughout her career that cultivated into her first full-length studio album.

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What does the title, Phoenix, mean to you?

I wrote this album about three and a half years ago. I rented out an Airbnb, and seven of us worked on it. We made two studios in two different rooms. I remember telling everyone that I wanted a transformation in my sound.

As an artist, everyone goes, "Well, who do you sound like?" Or, "What genre are you?" Musically, I'm just trying to sound like me.

My first EP, Blue Bird, was very melancholy. It has that blue color feeling to it. But with [Phoenix], I wanted it to have a lot of confidence. That was the only thing I said. The music could be love or breakup songs. We can write whatever it is that moves us, but it has to have some confidence in it.

Towards the end of that week-long writing group, I was like, "Wow, I really changed musically." This sounds like it has my stamp on it, but it's like a level up. That's initially why I did it.

Life happened. I went through a lot of really hard moments, and the album shifted. It became a metaphor for what was going on. For a long time, I didn't know how I was going to put out Phoenix since everything changed. I didn't know what the story would be, but in reality, it was all right there in front of me. I'm a person going through a difficult time and coming out stronger. Someone who has grown and learned.

How would you say that growth is represented throughout this album — is it in the songwriting? The visuals?

All of it! It's almost like Shakespeare, where everything is written for you. You know, you don't have to do much with Shakespeare.

I was trying to find answers to how the music represented me for so many years. Like I said, I wrote it three years ago. What am I doing putting it out when I am a completely different person? 

I knew it was the album I've always wanted to make. And honestly, now, some of the songs hit harder or mean something else. It strikes a different chord, but that is what makes music so beautiful. If it's done in the right way, with emotion and passion, it's the type of album you can listen to, no matter what decade you're in. It'll still move you, make you dance, make you cry. I'm excited to perform it and have it out because it's going to be such a great release for me.

A tour, maybe?

Yeah, yeah. In the future for sure.

When you listen to it, it's really important that you hear these incredible musicians. Samora Pinderhughes really goes in on a lot of these tracks. Beautiful outros. We've got horns on some of them.

It's an album that feels alive. I remember thinking how much I would enjoy performing it with the live instruments and a full band. That's what excites me as an artist.

The lead single, "Brighter," features Kevin Garrett. How did that come about? And why did you think that track would be the perfect song to lead the new era?

Kevin was a part of the writing camp that was there for seven days, and "Brighter" was one of my favorite songs off that album. I wanted to create a super funky beat. I got this rimshot that reminds me of some track on D'Angelo's Voodoo. It's got this kind of classic, in-the-pocket, fun moment to it. Musically, aesthetically, it was one of the songs that made my neck pop every time I would listen to it. I wanted to start the era with something that brought me so much joy.

In the music video, I'm on a horse. Then, people's flip phones blow up, and I leave the party. Eventually, I turned into a phoenix. The party represents my old life — I left to come to Los Angeles. Running into the streets and turning into a phoenix is the journey of healing and growth.

Stylistically, the music video for "Brighter" is very similar to your other single, "Baby I Can't Give You Up." Is there a connection between those two songs? Are the women in those music videos the same character?

"Baby I Can't Give You Up" is a love story, but it changed for me.

Listen, you can hear the songs and interpret them any way you want. That's what it's for. But in a music video, you see what it meant to me at that moment. Yes, it did start as a love song, but then it became a love letter to my family and friends.

I'm walking around London, which is where I was born. I'm half English, and a lot of my family lives there. I'm reminiscing through the hard times and who was there for me. Who poured me with so much love. At the end, there's a beautiful montage of my father, who passed away last year. Then, I hop on the train to my next journey.

You could say it's the same character, but she represents all the different points in my life.

Though this album is described as neo-soul and R&B, I hear influences of jazz, country, and more. How did you develop this unique fusion of genres?

I listen to so many different types of music. If you look at my saved songs on Spotify, it's Beyoncé, Solange, Radiohead, Enya, Stevie Wonder, and Prince. It's never-ending.

How I write my music… I don't really come up with a melody or lyrics first. I like to start from the beginning and be there throughout the whole process. So, I listen to the sound first, whatever it is that starts — a piano line, bassline, trumpets, or guitar. We come up with that, then the music. And that could be anything. Maybe, a chord strikes me. Like, Oh my god, I love that. Stay there.

I remember when I was 10, listening to Voodoo on my Walkman while I rode the school bus. People would be like, "What are you listening to?" It's D'Angelo. No one knew who that was because we were so young. I've always taken a different path when it comes to music. Again, it goes back to me trying to find my sound and what I like. That's really important to me. 

I have so much respect for music and musicians. That's why Prince is one of my favorite artists because he might be listed under R&B or pop, but we know he's more than that. He's his own genre. That's how I looked at this album — we didn't have to fit into any box. 

That was the beautiful thing about that writing camp was because we were like, "Whatever comes out, just let it come out." If I like it, I like it. If I don't, I don't, and we can move on or try to work with it. But I'm not trying to put anyone into a box. It's one of my favorite ways to write. I don't know how I'll go back to a regular day of writing in the studio. 

I recommend [any artist] to go somewhere, get up early in the morning, and write until like 2 or 3 a.m. Then, you do it again. It was so fulfilling to go back and forth between those two rooms. You're just leaning on each other. That journey to getting to where it is now was awesome.

How does 10-year-old Jasmine discover D'Angelo?

My parents! My mom is a jazz singer. My dad was a jazz aficionado. I grew up around a lot of musicians in my life. I was in theater because my dad was an actor, and I would go to my mom's gigs. I found out a lot through my parents. 

I also always listened to the radio. So, I would still know what's going on as a kid, but my mom had the dopest music setup in her house. She had shells and shells of records, cassette tapes, and CDs. And she had a piano with these speakers from the '80s that were amazing. She had headphones you could plug into them, so I would come home every day, do my homework, and sit in that corner for hours, going through her collection.

I went to performing arts school starting in middle school. I remember trying to figure out what to use as my audition song, and I found Stevie's Innervisions. At 11, I decided that "Living for the City" would be my audition song. I used that in middle school, at LaGuardia High School for vocal, and for the Berklee College of Music. And I got into all of them. All of that happened because I just saw and discovered on my own, which I thought was really cool.

In middle school, I sang Ella Fitzgerald's scat song, "Rockin' in Rhythm," and I remember the music teacher being like, "Wait, what? Where did you learn this?" I've always been an oddball, or whatever you want to call it. I just had a love for great music. So, when it comes to my music, I want to put out everything I've been influenced by. That's why some of the songs go on longer than usual. They'll have these amazing transitions, kind of like Earth, Wind & Fire or Prince, and that brings me joy.

You've experimented with so many different lanes, from musical theater to opera. But did you always want to try songwriting?

I didn't consider myself a songwriter for a long time because I didn't do it. As a teenager, I met with a couple of producers, and they'd always ask, "Who do you want to sound like?" It was more their project, so they wanted me to sound a certain way. Because of that, it didn't speak to me.

It wasn't until I was with Samora [that I had the freedom to express my ideas]. We wrote this song "Wild Thing" that is on my EP, Blue Bird. If I'm trying to fit somebody else's box, I'm not going to be able to write. But Samora taught me that I do have melodies and ideas for basslines — and I do have a lot to say.

Did that level of trust also introduce you to producing?

One of my favorite things to do after I finish the melodies and songwriting is sit with the producer. We go through everything. 

"Cali" started with my idea for a bassline and a horn section. So, I sat with my producer and gave them ideas and my input. If I can be there. I want to see it all through.

Does your vocal performance differ when you're auditioning and acting as a character versus your original music?

In musical theater, you're always playing a character. Whoever that character is, you're embodying that and decide what sound comes out of your mouth. On top of that, you're projecting and using your diaphragm differently because a packed theater of 1,300 people has to hear you.

When I sing my music, I get to be more vulnerable. I'm not embodying anyone but myself, so I get to experiment. In a lot of those songs, I go into the stratosphere with my head voice because in high school, I was training to be a coloratura soprano opera singer and learned how to sing crazy high in the clouds, like in my song "Cali."

It's fun to record and explore the different parts of my voice that I wouldn't normally use in a musical theater setting. All the different tones, tambours, and colors in my voice. I get to decide what I can do.

Is there a track on Phoenix that's particularly special to you?

There's an interlude called "Phoenix," and my dad is on it. Before he passed, I randomly asked, "Hey, could you send me a voicemail of what 'phoenix' means to you?" He sent me a three-minute voicemail, and we chopped it up into an interlude. He got to be a part of it, which is so beautiful.

Kate Hudson Is A Singer Now — And She Doesn't Care What You Think

Puerto Rican rapper Residente wants to embark on new adventures.  

The artist born René Pérez Joglar has dreams of directing movies and acting, writing books, and making for pleasure — not to pay the bills. These goals reflect a new attitude, one resulting from time spent reflecting on the passage of time and the presence of death.

Residente's sophomore album, Las Letras Ya No Importan (Lyrics No Longer Matter), echoes this transitory period. An extensive body of work, featuring 23 tracks, with several songs surpassing the five-minute mark. Las Letras is an act of deeply intimate rebellion.

"It’s a very personal album, and I sought to connect with myself in many moments throughout," Residente tells GRAMMY.com. 

While Las Letras explores topics already a hallmark of his music — the music industry, political systems, Puerto Rico — it's also exceedingly vulnerable. The 28-time Latin GRAMMY and four-time GRAMMY winner opens up about depression and personal relationships, and confronts mortality.

Lead single "313" is inspired by Residente's late friend Valentina, whose voice appears in the first interlude. As Residente recounted to El País of Spain and GQ Spain, Valentina was a violist, and the last messages they exchanged on WhatsApp were at 3:13.

The song begins with a French verse, fulfilling Valentina’s wish, expressed in the first interlude, to do something in that language. "Les paroles n'ont pas d'importance," (words no longer matter), a female voice whispers, followed by a spectacular string arrangement.

Residente revisited older works during this period of creative transition, and the record features previously released tracks  "René," "This Is America," and "Quiero Ser Baladista."

 Las Letras Ya No Importan features many collaborations, with actress Penélope Cruz, Spanish singer Silvia Pérez Cruz, Rauw Alejandro, Ricky Martin, Christian Nodal, Arcángel, Jessie Reyez and others making appearances. Hip-hop icon Busta Rhymes is featured on "Cerebro," while Big Daddy Kane makes an appearance on "Estilo Libre" with Vico C.

GRAMMY.com spoke with Residente via Zoom about the process that led him to his second album, the symbolism behind "313" and the artistic connection to Spain.  

This interview has been edited for length and clarity.

What inspired you to create Las Letras Ya No Importan?

It’s an album that marks a musical transition for what’s coming for me. It feels diverse; it also has songs with which I may not feel as connected [to] now because several years have passed since I made them. There are newer songs with which I do connect, which have a bit more to do with the way I want to start working on my music in the future.

"René" is part of this album, even though it came out four years ago. This is an album I was going to release during the pandemic. 

We have "René," which is very personal; we have "313," which I also feel is personal; then "Ron en el piso," [a song about the passage] of time, the collaboration with Nodal ("Pólvora de Ayer") also touches on the theme of time, of enjoying everything.

You confront death in several songs. In "René," you sang about losing a friend; in "Ron en el piso," you see your funeral; and in "313," you draw inspiration from your late friend Valentina. What is it about death that inspires you?

It’s something I’ve been going through in recent years. I lost many people I love, and it made me much more reflective when it comes to understanding time, the things I want to do, and the things I’ve stopped doing.

That’s why I’m also transitioning to cinema. I’ve always wanted to make films, directing, being behind the scenes, not being on stage.  I’m crazy about dedicating myself entirely to that.

I discovered acting now in a movie I starred in [In the Summers] that won the Jury Award at Sundance. When I saw it, I didn’t know I was the protagonist until I watched it. [The film] encouraged me to follow that too, and I’m going to want to act, direct; I want to dedicate myself to that for a while fully.

The album has a lot of life, and even though the lyrics no longer matter, you still have much to tell. You already said the album is very personal, but how would you describe it?

I can describe it in two years, not right now. It’s transitional. That’s what happened with Calle 13; everything was a musical and lyrical change from the second album onwards.

Residente represented a fusion of world music and rap. Now, in this one, I’m using a lot of strings, cellos, and double bass. I’m going to experiment a lot with different instruments in different ways. I’m going to be creative without the need to balance the album.

What’s coming next doesn’t have that artistic pressure. The only artistic pressure I want to have is to do the highest I can, which happens organically, not feeling pressured but naturally.

I want to do art as I did in college [at Savannah College of Art and Design]. I was never thinking about people or trying to convince anyone, and I was completely free, and that’s what happened with "313." I had the freedom I always wanted to have.

There’s substantial symbolism in "313," from the faceless dancers, the color pink. What was your vision with the visuals?

The dancers represent time. Penélope [Cruz] can represent many things, from life to Valentina, my friend, who inspired me to make the song. Penélope controls me, holds me, flies me, brings me back, and then I decide to control my life and time. That’s why I raise my hands, and everyone raises them, and time is running out, and then you see a sunset.

Sunset marks the end of something. The colors of the costumes also have some dusk elements. You can see at the end when I’m disappearing; it fades and blends with the end of the sunset.

These are decisions I make that are both aesthetic and technical. I put masks on the dancers because I liked it aesthetically. It also helped me speed up the process with makeup. I had to find creative ways to maintain the video’s aesthetics and make everything more agile because in filming, everything is time, and I had little of it.

What’s the idea behind the song "Las Letras Ya No Importan?"The arrangement is magical, with a numerical sequence from one to eight in different languages and a voice spelling of the alphabet.

That was the initial track. Before "313," I had this idea that I dreamed of with some basic notes, and it turned into something big.

There’s a voiceover of Penélope [Cruz] that says that we were eight [people in the studio], we are on an 8th street in New York, in studio B, which, if you look at it, it resembles the number 8. Everything connected with eight and [that number] also at a time level can mark infinity. So, I connected all that with the immensity of letters and languages. That piece’s runtime is five minutes. I think it’s pleasurable. I like that music, which resembles what I want to do.

Leo Genovese, an excellent musician and musical genius, made the arrangements. I greatly respect him.

In "Cerebro," you showcase your skill and vocal speed; what was it like collaborating with Busta Rhymes, whose own flow is iconic?

We met, and he loved the concept of what I was working on. He was a very humble, good person to me. After we met in person and talked for a while, he went to write after I sent him everything I had written in English.

I created ["Cerebro"] a while ago…. That’s why I tell you that the album has several concepts that I had to let go of because it was too much, and a lot of time had passed. I had a previous concept when I released the song "René" [in 2020], which is why it’s on the album. [At that time] I was working with the brain waves of different animals and people, and I made music with those brain waves.

This song ["Cerebro"] is part of that, and that’s why it’s called "Cerebro." The album was originally going to go that route. Then I didn’t do it; maybe I’ll connect to it in the future because I loved that idea.

What has Spain meant to you? The country has been so prominent in the trailers you’ve released and in the collaborations in your latest songs.

I've been making frequent trips to Madrid. This past year, I was there a lot; I was more in Madrid than at home. I traveled, wrote, and filmed videos like "Problema cabrón" and "313."

 I grew up with Spanish cinema by Almodovar and a bunch of directors I admire, and I wanted to collaborate with the actors I grew up watching in movies.

This album has many personal elements, and cinema is very intimate for me. I saw [Penelope Cruz] in [the movie] Abre los ojos when I was a kid; working with her now is a dream. The same goes with Javier Cámara and Najwa (Nimri) [who is in the film] Lovers of the Arctic Circle by Julio Medem. I saw all these people, and now being able to collaborate with them, be friends with them, talk to them is a dream. Everything is very connected to my life.

Erick The Architect Steps Into A New World On 'I’ve Never Been Here Before'

Lin-Manuel Miranda has consistently been between worlds. 

Whether it was growing up spending the school year in Manhattan and summers in Puerto Rico; spending the early 2000s teaching seventh grade English by day while refining "In the Heights" at night; or translating parts of one of the most beloved musicals of all time into the language half of its characters would have actually spoken, Miranda has constantly been navigating a cultural and sonic divide.

But his most consistent bridging of worlds has been between Broadway and hip-hop, most notably via the groundbreaking "Hamilton." As someone equally well-versed in Sondheim and Biggie, Miranda is uniquely positioned to bring rapping to the stage, and vice-versa. 

Miranda will expound on this best-of-both-worlds mindset during a special segment on the once-in-a-lifetime "A GRAMMY Salute To 50 Years Of Hip-Hop" live concert special in which he'll give both musical theater and rap fans an inside look at how and when he fell in love with hip-hop. Airing Sunday, Dec. 10, at 8:30 p.m. ET/8 p.m. PT on the CBS Television Network and streaming live and on demand on Paramount+, "A GRAMMY Salute To 50 Years Of Hip-Hop" features exclusive performances from Public Enemy, Rick Ross, 2 Chainz, T.I., Gunna, Tyga, Too $hort, Latto, E-40, Big Daddy Kane, GloRilla, Three 6 Mafia, a highly anticipated reunion from hip-hop pioneers DJ Jazzy Jeff and the Fresh Prince, and many more. The two-hour special celebrates the impactful history of hip-hop and showcases the genre's monumental cultural influence around the world.

Below are five of the ways Lin-Manuel Miranda has bridged Broadway and hip-hop culture.

Convincing Stephen Sondheim That Rap Is The Future Of Musical Theater

Yes, musical theater's Shakespeare was aware of rap before he met Miranda. His character of the Witch in "Into the Woods" — originally brought to life by Bernadette Peters — spits some rhymes (he respectfully called his efforts an "imitation" of the genre). 

But in his 2011 memoir/book of lyrics Look, I Made a Hat, Sondheim revealed that Miranda was the one musical theater composer who might show others how to incorporate rap into the art form.

"I was never able to find another appropriate use for the technique [after 'Into the Woods'], or perhaps I didn't have the imagination to," he wrote. "Miranda does. Rap is a natural language for him and he is a master of the form, but enough of a traditionalist to know the way he can utilize its theatrical potential: he is already experimenting with it in a piece about Alexander Hamilton. This strikes me as a classic example of the way art moves forward: the blending of two conventional styles into something wholly original… It's one pathway to the future."

Starting Freestyle Love Supreme

Back in the early 2000s, during "In the Heights" rehearsals, then-recent college grads Miranda, Thomas Kail, and Anthony Veneziale used to loosen up by freestyling.

"Anthony would come in and distract us, 'Let's rap about our day!' . . . And we would just freestyle," Miranda recalled years later on "The Tonight Show." Soon, Veneziale had a second idea: they should do that in front of people. Thus, Freestyle Love Supreme was born.

The idea was simple: it was a mash-up (again with the bridge-building) between an improv troupe and a rap cipher. The extended crew of regulars and special guests eventually grew to include talents like "Hamilton" standouts Daveed Diggs and Christopher Jackson, and even Wayne Brady. The idea became so successful that FLS had its own Broadway show and Vegas residency, with Miranda still popping up frequently as a special guest. 

Making The Hamilton Mixtape

Miranda teamed up with Questlove to make "Hamilton" even more hip-hop with The Hamilton Mixtape. The project features not just covers of "Hamilton" songs by well-known pop artists, which would have been noteworthy enough. 

But more importantly for our concerns, it has a number of hip-hop reinterpretations of numbers from the show. Check out, for example, "Immigrants (We Get the Job Done)," by K'naan, Snow Tha Product, Riz MC, and Residente, which turns one line from the musical into an absolute banger. 

The project also features Nas, the Roots, Joell Ortiz, Busta Rhymes, Dave East, and many more. To make the whole thing even more hip-hop, it's mixed together by an actual mixtape DJ, J.Period. You can listen to him discuss his role here. 

Appearing On The Cover Of Complex With Chance The Rapper

By mid-2016, there were few rappers on the planet more perfectly positioned between success and innovation than Chance the Rapper. The Chicago emcee captured tastemakers with his exquisite 2013 mixtape Acid Rap, before jumping into the mainstream with the May 2016 release of Coloring Book. But before all that, he was just a kid who loved going to poetry open mics. 

So it made a certain kind of sense when Complex decided to pair him with Miranda for their June/July 2016 cover story. The two had a ton in common (and Chance, it turned out, was a huge "Hamilton fan" who would soon cover "Dear Theodosia" for The Hamilton Mixtape). But even more than their conversation, it was the mere fact of its public existence that ended up drawing Broadway and hip-hop a little bit closer together than they had been before that issue hit the stands.

Writing "Hamilton"

We saved the best — and most obvious — for last. Hamilton more than lived up to the potential to theatricalize rap that Sondheim saw in it. It showed that rapping could be a key, perhaps the key, part of a major musical, and that show could not only be great, but also be a giant, world-beating, Disney+-streaming hit. 

Its quotations and interpolations of classic rap songs served multiple purposes. They were in-jokes for the rap fans in the audience, an acknowledgement that this theater guy was one of us. They also provided Easter eggs for the Broadway set, a hope that maybe one day they would figure out that it wasn't originally Alexander Hamilton who described himself by saying, "I'm only 19, but my mind is old" or Thomas Jefferson who boasted, "If you don't know, now you know." 

Watch Backstage Interviews From "A GRAMMY Salute To 50 Years Of Hip-Hop" Featuring LL Cool J, Questlove, Warren G & E-40, And Many More

Once a marginalized genre associated with lewdness and criminality — much like the genres from which it draws so much influence, dancehall and hip-hop —  reggaeton is now firmly in the mainstream. While dominant across Latin America in the new millennium, reggaeton has made huge inroads with English-speaking audiences in the past decade, particularly with crossover hits like "Bailando," "Despacito," and numerous Bad Bunny songs from the past three years.

Although many associate reggaeton with Puerto Rico, the roots of the genre can be found in Panama, with artists like El General and Nando Boom taking Jamaican dancehall riddims — like dembow, first introduced in the Shabba Ranks song of the same name — and rapping in Spanish over them in the early 1990s. In Puerto Rico, early reggaeton was called "underground," and gained popularity in the mid-1990s through mixtapes put out by DJs like Playero and Negro, who utilized hip-hop techniques to alter the dancehall riddims as an instrumental track for local rappers and singers like Daddy Yankee.

Reggaeton has long been a male-dominated genre (with Ivy Queen being the main exception to the rule), but in recent years female singers have become more prominent. Colombian singer Karol G, for example, is currently one of the genre’s biggest stars, and Spanish singer Rosalía pivoted to reggaeton for her 2022 album Motomami, which won a Latin GRAMMY for Album Of The Year. 

Colombian artists have also been making their way to the top of the reggaeton charts in recent years — alongside Karol G, there’s J Balvin and Maluma — although Puerto Rican artists still dominate the genre, with current stars like Rauw Alejandro and Anuel AA.

Reggaeton will only continue to evolve and develop; read on for 10 songs that represent the sonic and cultural evolution of the genre in the past three decades.

El General - "Tu Pum Pum" (1990)

Years before the term reggaeton was invented, Panamanian rapper El General (Edgardo Franco) was the first artist to gain recognition recording reggae en español. Given the history of West Indian immigration to Panama to build the Canal, it’s not surprising that the story of reggaeton begins there. This proto-reggaeton style emulated Jamaican dancehall much more closely than later styles would. El General and his friends got started by taking Jamaican riddims like the genre-defining dembow and rapping in Spanish over them; they used to board buses in Panama City and perform for fellow riders. El General was known as a skilled improvisor.

He moved to New York to study in the late 1980s, and hooked up with fellow Panamanian and producer Michael Ellis, who is said to have invented the term "reggaeton." El General’s first hit, "Tu Pun Pun" is a Spanish-language version of Jamaican dancehall artist Little Lenny’s 1990 song "Punnany Tegereg" that’s quite faithful musically to the original. 

The title of the song is slang for female genitals, and the lyrics chronicle El General’s sexual prowess in graphic detail. Its chorus chants, "Your pum pum, baby baby, won’t kill (tame) me." The song became a hit in the U.S. and El General went on to have a successful, albeit brief, career. 

Tego Calderón - "Pa’ Que Retozen" (2003)

One of the biggest tracks on Tego Calderón’s debut album, El Abayarde, "Pa’ Que Retozen" was a party anthem and one of the first reggaeton hits in the U.S. It represents the culmination of many musical shifts that took place during the 1990s in Puerto Rico. By the mid-1990s, the dembow riddim began to dominate the Puerto Rican underground scene. As the millennium approached, DJs and producers began to incorporate elements of Latin popular music genres as well.

"Pa’ Que Retozen" is a good example of this trend, as bachata-style guitar riffs play underneath Calderón’s rapping. The background track switches up several times in this song, including an incredibly catchy, high-pitched synth riff heard in the second verse. Other tracks on El Abayarde also incorporate Latin genres and instruments — like bongó drums on "Abayarde," Afro-Puerto Rican bomba percussion on "Loíza," and a full salsa orchestra and vocals on "Planté Bandera."

Ivy Queen - "Quiero Bailar" (2002)

Known as the "Queen of Reggaeton," Ivy Queen was the only prominent female reggaeton artist for nearly two decades. She released two albums in the late 1990s, but it was her third album, Diva, in 2003, that really broke through. Ivy Queen intentionally wrote from a female perspective, as she had come up in a male-dominated scene in San Juan where women were constantly being objectified.

With her deep, throaty vocal tone, Ivy Queen proclaims on "Quiero Bailar" that although she wants to dance — even in the sexualized perreo style that had become synonymous with reggaeton — that doesn’t necessarily mean she wants to have sex with her dance partner. The song is still an important anthem for women who want to feel free to bump and grind and express themselves on the dancefloor without men expecting a sexual encounter. 

Don Omar - "Dile" (2003)

Three of the genre’s most influential artists exploded on the scene at roughly the same time: Calderón, Daddy Yankee and Don Omar, with the latter two involved in a rivalry for the title of "King of Reggaeton." However, Don Omar always stood out among the three for the lyricism of his voice — he was a more gifted singer than many of his peers.

His debut album, The Last Don, is considered to be a classic, utilizing a similar approach as Calderón of injecting more melodic Latin styles, like bachata and salsa, into his music. The Dominican production team Luny Tunes, who was instrumental in expanding the sound of reggaeton and distinguishing it further from its Jamaican roots,  produced about half the album’s tracks.

Like "Pa’ Que Retozen," Don Omar’s first major single, "Dile" relies heavily on a bachata guitar line, but his vocal style is quite different from the deep, resonant rapping of Calderón. The combination of Don Omar’s tenor voice with the melodic instrumentals of "Dile" makes for a very aesthetically pleasing, yet danceable song. In addition, he interpolates a salsa song, Joe Arroyo’s "La Noche," into a bridge-like section in the middle of "Dile." 

The subject matter is also more emotional than many reggaeton songs had been up to this point, as he’s pleading with a woman to tell her boyfriend that she wants to be with someone else (Don Omar).  

 Daddy Yankee - "Gasolina" (2004)

The first reggaeton song to be nominated for Record Of The Year at the Latin GRAMMYs, "Gasolina" still stands as the genre’s most iconic and recognizable song. The song catapulted not only Daddy Yankee into the mainstream, but also the genre itself. It appeared on Daddy Yankee’s third studio album, Barrio Fino, which broke numerous records and won many awards.

Barrio Fino took a broad approach, which proved incredibly successful. Many of the album’s tracks were produced by Luny Tunes, including its two biggest hits, "Gasolina" and "Lo Que Pasó, Pasó." The album also features a salsa-reggaeton fusion and an R&B-inflected rap song that sounds like it could have been recorded by Big Pun.

As for the concept behind "Gasolina," Daddy Yankee was living in a San Juan housing project with his family, where he often heard people on the street shouting, "iComo le gusta las gasolina!" ("How she likes gasoline!"), referring to women who accept rides from men with nice cars. He took that phrase and ran with it, creating the famous hook "A mí me gusta la gasolina, dame más gasolina" ("I like gasoline, give me more gasoline"). A decade later he laughed at the idea that the term "gasolina" referred to drugs — as many people assumed — claiming that he used it literally, to refer to cars. 

"Oye Mi Canto" - N.O.R.E., feat. Nina Sky, Gem Star, Daddy Yankee, and Big Mato

Reggaeton exploded in popularity in the mid-aughts, which explains why there are so many classic songs from that time period. "Oye Mi Canto" was the first collaboration between an American rapper (N.O.R.E.) and reggaeton artists, and included verses in English and Spanish.

The song originally featured Tego Calderón but Daddy Yankee replaced him in the video. It also signaled an acceptance of reggaeton by New York hip hop artists — Fat Joe also appears in the video. It peaked at No. 12 on the Billboard Top 100, a first for a reggaeton song.

The song utilizes a common feature of commercial hip hop at the time, a catchy R&B hook sung by a female vocalist, Nina Sky. The hook borrows from and adapts the recognizable chorus "Boricua, morena, Boricua, morena," which was heard on Big Pun’s massive 1998 hit "Still Not A Player," but extends it to include other Latino ethnicities beyond "Boricua" (Puerto Rican).

Calle 13 -"Atrévete-te-te" (2005)

Hardly a traditional reggaeton group, Calle 13 nonetheless created one of the genre’s most popular, beloved songs in 2005 with their irreverent hit "Atrévete-te-te." Rapper Residente and instrumentalist/producer Visitante, step-brothers, founded the group in 2004, and gained fame with a song about the FBI killing of Puerto Rican independence leader Filiberto Ojeda Ríos called "Querido FBI."

Residente is the most politically outspoken rapper within reggaeton, a genre the two musicians have tended to distance themselves from, preferring not to be labeled. The group’s music has always been eclectic, using live instrumentation and unusual timbres. These elements undoubtedly relate to the fact that Visitante plays dozens of instruments. The brothers still hold the record for most Latin GRAMMY Awards in history, a whopping 27 each!

"Atrévete-te-te" is an infectious cumbia-reggaeton hybrid featuring an unforgettable high-register clarinet. Residente’s lyrics are raunchy, witty, and replete with American pop culture references and anglicisms. He dares a "Miss Intellectual" to get down off her culturally elitist high horse and let loose: "I know you like Latin pop rock, but reggaeton gets into your intestines, under your skirt like a submarine, and brings out your ‘Taino’ (indigenous people native to Puerto Rico)." He reinforces his point later, singing, "Who cares if you like Green Day? Who cares if you like Coldplay?"

"Bailando" - Enrique Iglesias feat.Descemer Bueno and Gente de Zona (2014)

In the 2010s reggaeton’s popularity continued to grow, and "Bailando" was one of the songs that significantly raised the genre’s visibility among English-language audiences. Nonetheless, Spanish pop singer Enrique Iglesias originally didn’t like the song.

"Bailando" was written and recorded by Cuban singer/songwriter Descemer Bueno and Cuban reggaeton duo Gente de Zona, who had become one of the island’s biggest musical groups. When Iglesias heard Bueno’s recording, he changed his mind and they added his vocals. 

Garnering many awards, and winning Song of the Year at the 2014 Latin GRAMMYs, "Bailando" was flamenco-infused reggaeton designed for mass appeal. It follows a traditional pop song format, with Iglesias singing the verses and trading off with Gente de Zona and Bueno in the extended chorus sections. The lyrics are standard love song fare, and don’t include any of the rapped vocals or Cuban slang that had made Gente de Zona so popular in Cuba. Nonetheless, it peaked at No. 2 on the Billboard Hot 100 and spent a record-breaking 41 weeks at the top of the U.S. Latin charts. 

"Despacito" - Luis Fonsi featuring Daddy Yankee, with a remix feat. Justin Bieber (2017)

Love it or hate it, it’s impossible to ignore the cultural impact of "Despacito." It was already a huge hit in its original version, by Puerto Rican singer Luis Fonsi and Daddy Yankee. But when Justin Bieber called Fonsi up to inquire about doing a remix, it became 2017’s song of the summer.

Like "Bailando," the original version was already as much Latin pop as it was reggaeton, and although Daddy Yankee has some rapped vocals in the second verse, he’s mainly singing as well. The producers decided to use a Puerto Rican cuatro, which opens the song, in addition to an acoustic guitar in order to give the song a more local feel. One unique element was the insertion of a rhythmic break right before the chorus "Despacito" (which translates to "slowly") comes in. The way Fonsi breaks up the three syllables in the title word, taking his time with them, is a nice touch.

The Justin Bieber remix was released three months later, and maintained the song’s original rhythms and Daddy Yankee’s verses. An English verse was added for Bieber at the beginning of the song, and he sang the "Despacito" choruses in Spanish — the first time he’d ever sung in Spanish. It quickly rose to No. 1 on the Hot 100 charts, which gave Fonsi and Daddy Yankee their first No. 1 hit. It stayed at the top of the charts for 16 weeks, tying with "One Sweet Day," by Mariah Carey and Boyz II Men, and remained the longest-leading No. 1 single until 2019. "Despacito" also won Song and Record Of The Year at the Latin GRAMMYs.  

"Titi Me Preguntó" - Bad Bunny (2022)

Bad Bunny is not only the most prominent artist in contemporary reggaeton — he was the biggest artist in the world in 2022. It’s impossible to list all of the accolades Benito Antonio Martínez Ocasio has attained in his short career, but here are a few: His latest, Un Verano Sin Tí, was the first Spanish-language one to be nominated for Album Of The Year at the 2023 GRAMMYs, he's been Spotify's most streamed artist in the world for three straight years.

Un Verano Sin Tí was a masterful achievement, showcasing a wide variety of contemporary Latin music beyond reggaeton, including Dominican dembow and mambo, bachata, electro-cumbia, and even indie rock — all anchored by Bad Bunny’s emo vocal style. The album is a celebration of Spanish Caribbean identity, paying homage as much to Dominican as to Puerto Rican music.

"Titi Me Preguntó" is not only one of the album’s biggest hits, but also one of its most complex tracks, featuring several discrete sections. It begins with a bachata guitar intro, followed by Bad Bunny’s rapped vocals accompanied by a sparse backbeat. His aunt is asking why he goes out with so many girls and won’t settle down. The body of the song speeds way up, keeping a sparse accompaniment, as Bad Bunny lists the names and cities of different girlfriends. 

But there’s an interesting shift at the 2:15 mark, where the bachata guitar returns and we hear a woman’s voice admonishing him for being an f-boi. It’s followed by anguished Bad Bunny vocals singing, "I’d like to fall in love but I can’t." The music changes back to the sparse backbeat accompaniment when he sings: "I don’t even trust myself," and notes how many women say they want to have his first-born child. The singing returns, as a spooky electronica melody is added into the background mix: "Listen to your friend, I’ll only break your heart…I don’t know why I’m like this." 

This is a man struggling with interpersonal demons, and this vulnerable masculinity (and his past refusal to conform to rigid gender norms) is precisely why Bad Bunny is so beloved by his female fans.  

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